Acid-Catalyzed Hydrolysis of N-Phenyl-4-substituted-benzohydroxamic Acids

Article abstract of DOI:10.1021/jo00085a028

Acidity rate profiles have been established for the hydrolysis of some N-phenyl-4-substituted-benzohydroxamic acids 4-XC6H4(C=O)N(OH)C6H5 (X=H, CH3, OCH3, NO2, Cl, F) in sulfuric acid solutions in 20/80 (v/v) dioxane-water medium.Analysis of the data by the Cox-Yates excess acidity method and substitutent, temperature, and solvent isotope effects are all compatible with a changeover from an A-2 mechanism at low acidities to a predominantly A-1 mechanism at high acidities.